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Dichloromethane → Di[(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)-2,4,6,8-nonatetraenyl](2S)-2-[(tert-butoxycarbonyl)amino]butanedioate

HRID 1796879
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1796879
[C:1]([NH:8][C@H:9]([C:14]([OH:16])=[O:15])[CH2:10][C:11]([OH:13])=[O:12])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C(Cl)Cl.Cl.C(N=C=N[CH2:26][CH2:27][CH2:28]N(C)C)C.[CH3:32][C:33]1[CH2:38][CH2:37][CH2:36][C:35]([CH3:40])([CH3:39])[C:34]=1/[CH:41]=[CH:42]/[C:43](/[CH3:52])=[CH:44]/[CH:45]=[CH:46]/[C:47](/[CH3:51])=[CH:48]/[CH2:49]O>CN(C)C=O>[CH3:51]/[C:47](/[CH:46]=[CH:45]/[CH:44]=[C:27](\[CH3:26])/[CH:28]=[CH:41]/[C:34]1[C:35]([CH3:39])([CH3:40])[CH2:36][CH2:37][CH2:38][C:33]=1[CH3:32])=[CH:48]\[CH2:49][O:15][C:14](=[O:16])[C@@H:9]([NH:8][C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[CH2:10][C:11]([O:13][CH2:49]/[CH:48]=[C:47](\[CH3:51])/[CH:46]=[CH:45]/[CH:44]=[C:43](\[CH3:52])/[CH:42]=[CH:41]/[C:34]1[C:35]([CH3:40])([CH3:39])[CH2:36][CH2:37][CH2:38][C:33]=1[CH3:32])=[O:12]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 6344DichloromethaneHCID 99718N-(tert-butoxycarbonyl)-L-aspartic acidHCID 445354RetinolHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Produkt 1

HCID 86590977Di[(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)-2,4,6,8-nonatetraenyl](2S)-2-[(tert-butoxycarbonyl)amino]butanedioate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

N-Boc aspartic acid (1.2 mg), methylene chloride 20 ml and minimum amount of dimethylformamide (DMF) were added to nitrogen filled, three mouth- round bottom flask and melted. The reaction mixture was cooled down into 0° C., 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride [EDCI](1.36 g)were added slowly, and stirred for approximately 30 minutes. Retinol (0.51 g) was added into the reaction mixture, small amount of N,N′-dimethylaminopyridine (DMAP) were added immediately, and stirred for approximately 1˜3 hours. After the reaction was finished, eluent were removed under the low pressure, the residues were melted with ethyl acetate and washed several times with water and Brine. Organic phase were dried with anhydrous MgSO4, concentrated under low pressure and separated with column chromatography.

Aufarbeitung

  1. additionfilled
  2. additionwere added immediately
  3. stirringstirred for approximately 1˜3 hours
  4. customeluent were removed under the low pressure
  5. washwashed several times with water and Brine
  6. dry with materialOrganic phase were dried with anhydrous MgSO4
  7. concentrationconcentrated under low pressure
  8. customseparated with column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-cf1da0af55b84698803c304c84df7561
Quelldatensatz
uspto-grants-2006_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07030265B2

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